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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10HgO2S
Molecular Weight 382.83
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLMERCURITHIOSALICYLIC ACID

SMILES

CC[Hg]SC1=C(C=CC=C1)C(O)=O

InChI

InChIKey=HXQVQGWHFRNKMS-UHFFFAOYSA-M
InChI=1S/C7H6O2S.C2H5.Hg/c8-7(9)5-3-1-2-4-6(5)10;1-2;/h1-4,10H,(H,8,9);1H2,2H3;/q;;+1/p-1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.fda.gov/biologicsbloodvaccines/safetyavailability/vaccinesafety/ucm096228.htm | https://www.ncbi.nlm.nih.gov/pubmed/18049924 | https://www.ncbi.nlm.nih.gov/pubmed/10428009

Thimerosal is organomercury antiseptic and antifungal agent, used as a preservative in vaccines, immuloglobulins, nasal sprays, contact lens solutions. In USA, European Union countries thiomersal is no longer used in childhood vaccines due to public fears, although the FDA review of 1999 foud no evidence of harm from the use of thimerosal as a vaccine preservative, other than local hypersensitivity reactions. Thimerosal was used as a component of topical antiseptic solution and antiseptic ointment for treating cuts, nasal sprays, eye solutions, vaginal spermicides, diaper rash treatments, but re-evaluation of the drug in 1980-s demonstrated ineffectiveness and toxicity in topical pharmaceutical products, and topical thimerosal was withdrawn from the market. The mechanism of action of thimerosal has not been fully elucidated. It is believed that thimerosal inhibits sulfhydryl-containing active site of various enzymes and binds to sulfhydryl compounds, such as glutathione, cysteine, and SH groups of protein. In addition, thimerosal activates the InsP3 calcium channel on endoplasmic reticular membrane, thereby triggering the release of calcium from intracellular stores resulting in a calcium-induced calcium-influx of extracellular calcium. Consequently, thimerosal may induce or inhibit cellular functions dependent on calcium signaling.

CNS Activity

Curator's Comment: Mercury accumulates in the brain and is converted to inorganic mercury.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
AFLURIA

Approved Use

AFLURIA is an inactivated influenza virus vaccine indicated for active immunization of persons ages 6 months and older against influenza disease caused by influenza virus subtypes A and type B present in the vaccine.

Launch Date

2007
Primary
MERTHIOLATE

Approved Use

Thimerosal was used as a component of topical antiseptic solution and antiseptic ointment for treating cuts, nasal sprays, eye solutions, vaginal spermicides, diaper rash treatments
PubMed

PubMed

TitleDatePubMed
Homozygous gene deletions of the glutathione S-transferases M1 and T1 are associated with thimerosal sensitization.
2000 Aug
Biochemical and molecular basis of thimerosal-induced apoptosis in T cells: a major role of mitochondrial pathway.
2002 Aug
Dose-response study of thimerosal-induced murine systemic autoimmunity.
2004 Jan 15
Preservatives sensitivity in Israel: a 10-year overview (1995-2004).
2006 Oct
Cultured lymphocytes from autistic children and non-autistic siblings up-regulate heat shock protein RNA in response to thimerosal challenge.
2006 Sep
Thimerosal induces apoptosis and G2/M phase arrest in human leukemia cells.
2006 Sep
Thimerosal induces TH2 responses via influencing cytokine secretion by human dendritic cells.
2007 Feb
Thimerosal-induced apoptosis in human SCM1 gastric cancer cells: activation of p38 MAP kinase and caspase-3 pathways without involvement of [Ca2+]i elevation.
2007 Nov
Neurodevelopmental disorders, maternal Rh-negativity, and Rho(D) immune globulins: a multi-center assessment.
2008 Apr
Characterization of early events involved in human dendritic cell maturation induced by sensitizers: cross talk between MAPK signalling pathways.
2008 Aug 1
Thiol-modulated mechanisms of the cytotoxicity of thimerosal and inhibition of DNA topoisomerase II alpha.
2008 Feb
Mercury, vaccines, and autism: one controversy, three histories.
2008 Feb
Cleavage of focal adhesion kinase is an early marker and modulator of oxidative stress-induced apoptosis.
2008 Jan 10
Sensitizing potential of triclosan and triclosan-based skin care products in patients with chronic eczema.
2008 Oct
Neonatal administration of a vaccine preservative, thimerosal, produces lasting impairment of nociception and apparent activation of opioid system in rats.
2009 Dec 8
Expression of metallothionein mRNAs on mouse cerebellum microglia cells by thimerosal and its metabolites.
2009 Jun 30
Induction of metallothionein in mouse cerebellum and cerebrum with low-dose thimerosal injection.
2010 Apr
Occludin gene expression as an early in vitro sign for mild eye irritation assessment.
2010 Feb
Responsiveness of human monocyte-derived dendritic cells to thimerosal and mercury derivatives.
2010 Jul
Sensitization effect of thimerosal is mediated in vitro via reactive oxygen species and calcium signaling.
2010 Jul-Aug
Low molecular weight thiols reduce thimerosal neurotoxicity in vitro: modulation by proteins.
2010 Oct 29
Contact sensitization in very young children.
2011 Oct
Thimerosal-induced apoptosis in mouse C2C12 myoblast cells occurs through suppression of the PI3K/Akt/survivin pathway.
2012
Influence of environment exposures on the frequency of contact allergies in children and adolescents.
2012
Transcriptomic analyses of neurotoxic effects in mouse brain after intermittent neonatal administration of thimerosal.
2014 Jun
Thimerosal induces apoptotic and fibrotic changes to kidney epithelial cells in vitro.
2015 Dec
Functional and molecular effects of mercury compounds on the human OCTN1 cation transporter: C50 and C136 are the targets for potent inhibition.
2015 Mar
Patents

Patents

Sample Use Guides

As a component of vaccines, thimerosal is administered intramuscularly.
Route of Administration: Intramuscular
In Vitro Use Guide
Antimicrobial activity of thimerosal was determined using Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus and Candida albicans. The inoculum size was 10^6 oranisms/ml in each case. Antimicrobial activity was determined employing doubling diliutions of the test agents. MIC of thimerosal was 1.5 - 0.1 ug/ml.
Name Type Language
ETHYLMERCURITHIOSALICYLIC ACID
Common Name English
MERCUROTHIOLIC ACID
Common Name English
O-ETHYLMERCURITHIOBENZOIC ACID
Common Name English
MERCURATE(1-), ETHYL(2-(MERCAPTO-.KAPPA.S)BENZOATO(2-)-.KAPPA.O)-, HYDROGEN (1:1)
Common Name English
((O-CARBOXYPHENYL)THIO)ETHYLMERCURY
Common Name English
ELCIDE
Brand Name English
THIOMERSAL (ACID)
Common Name English
THIMEROSALA
Common Name English
MERSEPTYL
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 78902
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
Code System Code Type Description
DAILYMED
4071N4J64W
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY
PUBCHEM
67361
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-719-5
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY
RXCUI
1546427
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY RxNorm
CAS
148-61-8
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY
FDA UNII
4071N4J64W
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY
DRUG BANK
DB02731
Created by admin on Fri Dec 15 15:38:25 GMT 2023 , Edited by admin on Fri Dec 15 15:38:25 GMT 2023
PRIMARY